Ethyl trifluoroacetate → HCID 178522125, compound

HRID 520745Notes

Reaction equation

HRID 520745 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:16])([F:15])[C:10](OCC)=[O:11].CN(C1C=CC=CN=1)C>O1CCCC1>[F:8][C:9]([F:16])([F:15])[C:10]([N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1)=[O:11]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 104392-AminopyridineHCID 218852-Dimethylaminopyridine

Product 1

HCID 178522125HCID 178522125, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-aminopyridine in an amount of 0.94 g (10 mmol) was dissolved in 20 mL of tetrahydrofuran (THF), following which 2.84 g (20 mmol) of ethyl trifluoroacetate and 1.22 g (10 mmol) of dimethylaminopyridine were added, and refluxing was carried out for 22 hours. THF was removed by distillation, following which purification was carried out with a silica gel column (developing solvent: 4:1 solution of hexane and ethyl acetate), giving 0.26 g of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide (yield, 13.7%).

Workup

  1. additionwere added
  2. temperaturerefluxing
  3. customTHF was removed by distillation
  4. customwhich purification

Sources & evidence

ORD record
ord-58a77a39ec094a97a0b0ce86eb868e7f
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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